6,7-dichloro-1-(3,4,5-trimethoxybenzyl)isoquinoline | 762199-99-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 6,7-dichloro-1-(3,4,5-trimethoxybenzyl)isoquinoline
• 英文别名: 6,7-Dichloro-1-[(3,4,5-trimethoxyphenyl)methyl]isoquinoline
• CAS: 762199-99-5
• 化学式: C₁₉H₁₇Cl₂NO₃
• 分子量: 378.255
• InChiKey: KFRYQNXWQFJMGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6,7-dichloro-1-(3,4,5-trimethoxybenzyl)isoquinoline 在 盐酸 、 三氟化硼 作用下， 生成 6,7-dichloro-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  6,7-Dichloro-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline. A structurally novel .beta.-adrenergic receptor blocking agent

  摘要：

  Replacement of the catecholic hydroxyl groups of the beta-adrenergic receptor agonist 6,7-dihydroxy-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline (trimetoquinol) with chloro substituents results in a compound with marked beta-adrenoceptor antagonist properties. This, therefore, parallels the similar transformation of the beta-adrenoreceptor agonist isoproterenol into the antagonist dichloroisoproterenol. In a test for inhibition of isoproterenol-induced enhancement of the rate of contraction of spontaneously beating guinea pig atrial pairs the resultant 6,7-dichloro-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline (6b) had a KB value of (6.7 +/- 2.3) X 10(-8) M. Although this is nearly 2 orders of magnitude less potent than propranolol (KB = 6.2 X 10(-10) M in this test), this compound represents the prototype of a new class of beta-adrenergic receptor blockers, and unlike dichloroisoproterenol it is not a partial agonist. It has physicochemical properties, e.g., pKa and distribution and partition coefficients, that differ from the prototypic beta-blockers. These altered properties might impart advantageous tissue distribution and altered pharmacological properties to the new molecule. This new beta-adrenoreceptor antagonist is suggested to merit further study.

  DOI：

  10.1021/jm00161a039
• 作为产物：
  描述：

  6,7-dichloro-1-cyano-1,2-dihydroisoquinoline 在 sodium hydroxide 、 苄基三乙基氯化铵 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 6.5h， 生成 6,7-dichloro-1-(3,4,5-trimethoxybenzyl)isoquinoline
  参考文献：
  名称：

  6,7-Dichloro-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline. A structurally novel .beta.-adrenergic receptor blocking agent

  摘要：

  Replacement of the catecholic hydroxyl groups of the beta-adrenergic receptor agonist 6,7-dihydroxy-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline (trimetoquinol) with chloro substituents results in a compound with marked beta-adrenoceptor antagonist properties. This, therefore, parallels the similar transformation of the beta-adrenoreceptor agonist isoproterenol into the antagonist dichloroisoproterenol. In a test for inhibition of isoproterenol-induced enhancement of the rate of contraction of spontaneously beating guinea pig atrial pairs the resultant 6,7-dichloro-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline (6b) had a KB value of (6.7 +/- 2.3) X 10(-8) M. Although this is nearly 2 orders of magnitude less potent than propranolol (KB = 6.2 X 10(-10) M in this test), this compound represents the prototype of a new class of beta-adrenergic receptor blockers, and unlike dichloroisoproterenol it is not a partial agonist. It has physicochemical properties, e.g., pKa and distribution and partition coefficients, that differ from the prototypic beta-blockers. These altered properties might impart advantageous tissue distribution and altered pharmacological properties to the new molecule. This new beta-adrenoreceptor antagonist is suggested to merit further study.

  DOI：

  10.1021/jm00161a039

文献信息

• KAISER C.; OH HYE-JA; GARCIA-SLANGA B. J.; SULPIZIO A. C.; HIEBLE J. P.; +, J. MED. CHEM., 29,(1986) N 11, 2381-2384
  作者：KAISER C.、 OH HYE-JA、 GARCIA-SLANGA B. J.、 SULPIZIO A. C.、 HIEBLE J. P.、 +

  DOI：——

  日期：——